US4427670A - Skin preparation - Google Patents
Skin preparation Download PDFInfo
- Publication number
- US4427670A US4427670A US06/347,557 US34755782A US4427670A US 4427670 A US4427670 A US 4427670A US 34755782 A US34755782 A US 34755782A US 4427670 A US4427670 A US 4427670A
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- US
- United States
- Prior art keywords
- skin
- phosphatide
- ointment
- preparation
- preparations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
Definitions
- This invention relates to a skin preparation and more particularly to a skin preparation exerting an improved therapeutic activity of a topical corticosteroid present therein.
- Topical corticosteroid-containing skin preparations have heretofore been used widely. However, it is still desired to improve the efficacy of these skin preparations.
- this invention resides in a skin preparation which contains (i) a phosphatide, (ii) a topical corticosteroid and (iii) butylhydroxyanisole and/or butylhydroxytoluene.
- the phosphatides which can be used in the skin preparations of this invention include phosphatidylcholine (lecithin), phosphatidylethanolamine (cephlin), phosphatidylserine, phosphatidylinositol, phosphatidic acid and the like. Of course, a mixture of two or more of these phosphatides may be used. In such cases, it was found that the phosphatidylcholine content of the phosphatide mixture is most preferably between 10% and 40%. This is presumed to have relation to the fact that such phosphatidylcholine content is close to the phosphatide composition of the epidermis.
- soy phosphatide soy lecithin
- egg phosphatide egg lecithin
- soy phosphatide is particularly preferred.
- These commercially available phosphatides contain various phosphatides and in addition some substances other than phosphatides. The amount of such commercially available phosphatide to be used should be calculated based on the total phosphatide content thereof.
- the amount of phosphatides or phosphatide mixture used in the skin preparation of this invention depends on the diseases to which the skin preparation is applied, formulation, type and amount of the topical corticosteroid and the like, and is usually in the range of 0.1% to 30%, preferably 0.1% to 10%, more preferably 0.2% to 7% and most preferably 0.5 to 5% by weight based on the total weight of the preparation.
- the amount of phosphatide used is too low, the desired results of this invention will be attained insufficiently.
- the use of more phosphatide than required will not improve the desired results in a manner proportional to the amount of phosphatide, and bring about undesirable effects such as stickiness of the skin. For this reason, the above-mentioned range is preferred.
- the amount of the topical corticosteroid to be added should be determined on the basis of the strength of activity and the intended use of the particular corticosteroid. When a larger amount of the topical corticosteroid is added, it is preferred to increase the amount of the phosphatide added.
- the topical corticosteroid can be added as a solution dissolved in an oil phase component, or propylene glycol, polyethylene glycol, ethanol or the like. Alternatively, solid powder of the corticosteroid may be added and dispersed as such or after it is finely pulverized.
- the skin preparation of this invention contains butylhydroxyanisole and/or butylhydroxytoluene along with the aforementioned phosphatide and topical corticosteroid.
- butylhydroxyanisole and/or butylhydroxytoluene prevents very satisfactorily the phosphatide from coloring and keeps the skin preparation very stable for a prolonged period of time. Particularly, a combined use of both these compounds provides satisfactory results.
- predissolution of the topical corticosteroid in propylene glycol is preferred in view of solubility and mild irritation to the skin, but this suffers from instability with elapse of time.
- a highly stable ointment can be obtained by dissolving the corticosteroid in propylene glycol in which butylhydroxyanisole has been dissolved, because butylhydroxyanisole in soluble in propylene glycol.
- aqueous mixtures such as a solution, colloidal solution, emulsified lotion, O/W cream (hydrophilic cream) and aqueous gel wherein the aqueous phase is the continuous one
- oily mixtures such as a solution, ointment, W/O cream, gel base [e.g.
- Plastibase® (a mineral oil gelled with polyethylene, i.e., a gel of polyethylene and liquid paraffin)], absorption ointment in which an emulsifier is added to the oil and hydrophilic ointment wherein the oil phase is the continuous one; and non-aqueous, water-soluble bases such as a mixture of polyethylene glycol.
- a suspension base such as a shaking lotion in which a solid dispersing agent is added can also be prepared.
- Oily components, emulsifiers, dispersing agents, gelatinizers and solid materials which can be used to prepare such formulations are well known as those used in the preparation of cosmetics and topical products.
- the oily components include hydrocarbons such as liquid paraffin, vaseline, solid paraffin, microcrystalline wax, etc.; higher aliphatic alcohols such as cetyl alcohol, hexadecyl alcohol, stearyl alcohol, oleyl alcohol, etc.; esters of higher fatty acids with higher alcohols such as beeswax, spermaceti, etc.; esters or higher fatty acids with lower alcohols such as isopropyl myristate, isopropyl palmitate, etc.; vegetable oils, modified vegetable oils, hydrous lanolin and its derivative, squalene, squalane; higher fatty acids such as palmitic acid, stearic acid, etc. and the like.
- hydrocarbons such as liquid paraffin, vaseline, solid paraffin, microcrystalline wax, etc.
- higher aliphatic alcohols such as cetyl alcohol, hexadecyl alcohol, stearyl alcohol, oleyl alcohol, etc.
- Emulsifiers and dispersing agents which can be used include anionic, cationic and nonionic surfactants.
- Nonionic surfactants are preferred because of their low levels of irritation to skin.
- Typical of nonionic surfactants are fatty acid monoglycerides such as glyceryl monostearate, etc.; sorbitan fatty acid esters such as sorbitan monolaurate; etc.; sucrose fatty acid esters; polyoxyethylene fatty acid esters such as polyoxyethylene stearate, etc.; and polyoxyethylene higher alcohol ethers such as polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, etc.
- a polyoxyethylene fatty acid ester is advantageous in that the emulsion stability is highly improved.
- Particularly preferred for this purpose are those polyoxyethylene fatty acid esters wherein the fatty acid contains usually about 8 to 26 carbon atoms, preferably about 12 to 18 carbon atoms and the number of ethylene oxide molecules in the addition polymerized polymer chains (or degree of addition polymerization of ethylene oxide) is usually about 20 to 60, preferably about 40 to 55.
- An example of such ester is polyoxyethylene monostearate.
- Gelatinizers include carboxymethylcellulose, cellulose gel, carbopol, polyvinyl alcohol, polyethylene glycol and various gums.
- oily components emulsifiers, dispersing agents and gelatinizers, of course, can be used alone or in combination with each other.
- a chelating agent an antiseptics and the like, as required.
- the chelating agents which can be used include EDTA (ethylenediamine tetracetate), thioglycolic acid, thiolactic acid, thioglycerine and the like.
- the antiseptics which can be used include methyl, ethyl, propyl and butyl esters of p-hydroxybenzoic acid, o-phenylphenol, dehydroacetic acid and the salts thereof, p-chloro-m-cresol, p-chloro-m-xylenol and the like.
- pH of the skin preparation by adding citric acid, lactic acid, tartaric acid or the like.
- the pH value which should be adjusted to is dependent upon the stability of the skin preparation. In general, it is preferred that the skin preparation be slightly acidic to slightly alkaline. A fragrance may be added in a slight amount, if desired.
- one or more drugs selected from antibiotics, antihistaminics, antimycotic agents and vitamines may be incorporated into the skin preparation of this invention to prepare a compounded preparation.
- the skin preparations according to this invention exerts a markedly improved activity of the topical corticosteroid present therein, they can be used in the treatment of skin diseases including eczema, ichthyosis, lichen and psoriasis to attain the disappearance or alleviation of the sympton.
- the skin preparations of this invention disperse and retain the active ingredient, corticosteroid, in the skin for a prolonged period of time without loss of the corticosteroid so that they can exert the effect of the steroid effectively.
- the skin preparations are stable with little coloration or other change after the elapse of time.
- the skin preparations of this invention possess higher antiinflammatory activities as campared with topical corticosteroid preparations prepared with conventional ointment bases.
- Topical corticosteroid-containing skin preparations having the compositions given in Table 3 below were prepared.
- the test was carried out according to the Fujimura et al method.
- a 1% solution of ⁇ carrageenin dissolved in the Krebs solution is used as a phlogistic solution.
- the abdominal hair of the rats is completely removed using a hair clipper and a depilatory cream.
- the rats Five hours after the application, the rats are sacrificed by exsanguination and the abdominal skin are excised and reversed to measure the shortest and longest diameters of the blue areas.
- the edema areas are then punched out with a 17 ⁇ 17 mm skin punch and their wet weights are measured to give indices of the skin edemas.
- the soy phosphatide used in the test contained 30 to 32% phosphatidylcholine based on the total phosphatide content of the soy phosphatide.
- Topical corticosteroid-containing skin preparations having the compositions given in Table 5 below were prepared.
- the skin preparation of this invention possesses a higher antiinflammatory activity as compared with the comparative skin preparation prepared with conventional ointment bases, as evaluated by the rat croton oil ear edema test.
- Topical corticosteroid-containing skin preparations having the compositions given in Table 7 below were prepared.
- Example 11 contained butylated hydroxytoluene, while that of Comparative Example H was free from the same.
Abstract
Description
TABLE 1 __________________________________________________________________________ Example No. Compar- Compar- Compar- Compar- Example Example ative Example Example ative Example ative Example ative 1 2 A 3 4 B 5 C 6 D Formulation Oleagenous anhydrous Oleagenous an- ointment O/W cream hydrous ointment O/W cream Composition % % % % % % % % % % __________________________________________________________________________ Fluocinolone 0.025 0.025 0.025 0.025 0.025 0.025 -- -- -- -- acetonide Hydrocortisone acetate -- -- -- -- 13 -- 1.0 1.0 1.0 1.0 Soy phosphatide 4.0 2.0 -- 4.0 2.0 -- 4.0 -- 4.0 -- White petrolatum -- 87.945 -- 9.9 9.9 9.9 89.975 93.975 9.9 9.9 Liquid paraffin -- 5.0 -- 12.9 12.9 12.9 5.0 5.0 12.9 12.9 Plastibase ® 50W 95.95 -- 99.95 -- -- -- -- -- -- -- Butylated hydroxytoluene 0.025 0.025 0.025 0.025 0.05 0.025 0.025 0.025 0.025 0.025 Butylated hydroxyanisole -- 0.005 -- -- -- -- -- -- -- -- Stearyl alcohol -- -- -- 5.0 2.1 5.0 -- -- 5.0 5.0 Cetyl alcohol -- -- -- 2.1 5.0 2.1 -- -- 2.1 2.1 Polyoxyethylene -- -- -- 4.0 -- 1.7 -- -- 1.7 1.7 cetyl ether Polyoxyethylene -- -- -- -- 4.0 -- -- -- -- -- monostearate Ethyl p-hydroxybenzoate -- -- -- 0.1 0.1 0.1 -- -- 0.1 0.1 Methyl p-hydroxybenzoate -- -- -- -- 0.2 -- -- -- -- -- Butyl p-hydroxybenzoate -- -- -- 0.1 0.1 0.1 -- -- 0.1 0.1 Propylene glycol -- 5.0 -- -- -- -- -- -- -- -- Purified water -- -- -- 61.85 63.625 68.15 -- -- 63.175 67.175 Total (% by weight) 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 __________________________________________________________________________
TABLE 2 ______________________________________ Effects on mouse croton oil ear edema Edema Inhibition Example ratio ratio Drug No. Formulation (%) (%) Effect* ______________________________________ Fluocino- Example 1 Oleagenous 21.8 83.6 +++ lone Example 2 anhydrous 24.1 81.9 +++ acetonide Compara- ointment 40.1 69.9 ++ tive A Example 3 O/W cream 30.5 77.1 +++ Example 4 31.4 76.4 +++ Compara- 54.8 58.9 ++ tive B Hydro- Example 5 Oleagenous 35.6 73.3 +++ cortisone Compara- anhydrous 52.1 60.9 ++ acetate tive C ointment Example 6 O/W cream 37.0 72.2 +++ Compara- 53.8 59.6 ++ tive D Untreated -- 133.3 -- -- ______________________________________ *Score Inhibition Ratio +++ 70-100% ++ 40-70% + 10-40% ± 0- 10% ______________________________________
TABLE 3 __________________________________________________________________________ Compar- Compar- Example ative Example Example ative 7 E 8 9 F Formulation Oleagenous an- Absorption Macrogol hydrous ointment ointment ointment Composition % % % % % __________________________________________________________________________ Densonide 0.1 0.1 0.1 -- -- Methylprednisolone -- -- -- 1.0 1.0 acetate Soy phosphatide 4.0 -- 4.0 4.0 -- White petrolatum -- -- 40.0 -- -- Liquid paraffin -- -- -- 10.0 -- Macrogol 4000 -- -- -- 41.0 48.0 Macrogol 400 -- -- -- 43.95 50.975 Plastibase ® 50W 95.875 99.875 -- -- -- Butylated hydroxy- 0.025 0.025 0.025 0.025 0.025 toluene Cetyl alcohol -- -- 18.0 -- -- Sorbitan sesquioleate -- -- 5.0 -- -- Polyoxyethylene -- -- 0.5 -- -- lauryl ether Ethyl p-hydroxy- -- -- 0.1 -- -- benzoate Butyl p-hydroxy- -- -- 0.1 -- -- benzoate Purified water -- -- 32.175 -- -- Total (% by weight) 100.0 100.0 100.0 100.0 100.0 __________________________________________________________________________
TABLE 4 __________________________________________________________________________ Effects on Rat Carrageenin Edema Inhibi-.sup.(2) Inhibi- Inhibi- Mean In- Edema.sup.(1) tion Edema.sup.(3) tion Blue tion hibition Example Weight ratio ratio ratio area ratio ratio Overall.sup.(4) Drug No. Formulation (mg) (%) (%) (%) (mm.sup.2) (%) (%) effect __________________________________________________________________________ Desonide Example 7 Oleagenous 60.8 51.4 81.1 46.2 70.8 46.1 47.9 ++ Compara- anhydrous 75.2 39.9 100.3 33.4 82.9 36.9 36.7 + tive E ointment Example 8 Absorption 62.5 50.1 83.3 44.7 72.2 45.1 46.6 ++ ointment Methylpred Example 9 Macrogol 50.4 59.7 82.2 45.5 79.8 39.3 48.2 ++ nisolone Compara- ointment 60.6 51.6 98.9 34.4 88.9 32.3 39.4 + acetate tive F Untreated -- 125.7 -- 150.7 -- 131.4 -- -- -- __________________________________________________________________________ .sup.(1) Edema weight = Edema skin weight - Normal skin weight .sup.(2) Inhibition ratio = (Measured value when treated with ointment - Measured value when untreated) / (Measured value when untreated) × 100 .sup.(3) Edema ratio = (Edema skin weight / Normal skin weight) × 100 .sup.(4) Overall effect was evaluated from the mean inhibition ratio for the edema weight, edema ratio and blue area when treated with ointment.
Score Inhibition ratio ++ 40-60% + 20-40% ± 0-20%
TABLE 5 ______________________________________ Example 10 Comparative G Formulation Oleagenous anhydrous ointment Composition % % ______________________________________ Fludroxycortide 0.12 0.12 Soy phosphatide 4.0 -- White petrolatum 78.855 82.855 Liquid paraffin 5.0 5.0 Purified lanolin 4.0 4.0 Butylated hydroxytoluene 0.025 0.025 Stearyl alcohol 8.0 8.0 Total (% by weight) 100.0 100.0 ______________________________________
TABLE 6 ______________________________________ Effects on rat croton oil ear edema Edema ratio Inhibition ratio Example No. (%) (%) Effect* ______________________________________ Example 10 35.6 64.9 ++ Comparative G 50.1 50.6 ++ Untreated 101.4 -- -- ______________________________________ *The scores are the same as described in Table 2.
TABLE 7 ______________________________________ Example 11 Comparative H Formulation O/W cream Composition % % ______________________________________ Fluocinolone acetonide 0.025 0.025 Soy phosphatide 2.0 2.0 White petrolatum 9.9 9.9 Liquid paraffin 12.9 12.9 Stearyl alcohol 2.1 2.1 Cetyl alcohol 5.0 5.0 Polyoxyethylene monostearate 4.0 4.0 Ethyl p-hydroxybenzoate 0.1 0.1 Butyl p-hydroxybenzoate 0.1 0.1 Butylated hydroxytoluene 0.025 -- Purified water 63.85 63.75 Total (% by weight) 100.0 100.0 ______________________________________
TABLE 8 ______________________________________ Example Item Storage period at 40° C. No. observed 1 week 4 weeks 8 weeks 12 weeks ______________________________________ Example Surface - - - - 11 coloration Separation - - - - Compar- Surface - + ++ ++ ative coloration H Separation - - ± ± ______________________________________ Score ++ Significant change + Change ± Indistinct change - No change ______________________________________
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3945080A JPS56135416A (en) | 1980-03-27 | 1980-03-27 | Pharmaceutical preparation for skin |
JP55-39450 | 1980-03-27 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/243,430 Continuation-In-Part US4333927A (en) | 1980-03-27 | 1981-03-13 | Skin preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
US4427670A true US4427670A (en) | 1984-01-24 |
Family
ID=12553361
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/243,430 Expired - Fee Related US4333927A (en) | 1980-03-27 | 1981-03-13 | Skin preparation |
US06/347,557 Expired - Fee Related US4427670A (en) | 1980-03-27 | 1982-02-10 | Skin preparation |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/243,430 Expired - Fee Related US4333927A (en) | 1980-03-27 | 1981-03-13 | Skin preparation |
Country Status (5)
Country | Link |
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US (2) | US4333927A (en) |
JP (1) | JPS56135416A (en) |
DE (1) | DE3111767A1 (en) |
FR (1) | FR2478999A1 (en) |
GB (1) | GB2074027B (en) |
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US4701471A (en) * | 1986-04-16 | 1987-10-20 | Loucks Sr Joseph | Skin care composition |
US4711906A (en) * | 1984-12-21 | 1987-12-08 | Merckle Gmbh | Liquid diclofenac preparations |
US4784849A (en) * | 1983-08-15 | 1988-11-15 | Tutsky Ronald J | Skin care and shaving compositions |
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Also Published As
Publication number | Publication date |
---|---|
DE3111767A1 (en) | 1982-03-11 |
FR2478999A1 (en) | 1981-10-02 |
GB2074027B (en) | 1985-02-13 |
JPS56135416A (en) | 1981-10-22 |
US4333927A (en) | 1982-06-08 |
GB2074027A (en) | 1981-10-28 |
FR2478999B1 (en) | 1985-04-26 |
JPS6323971B2 (en) | 1988-05-18 |
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